


Girls At Night

by stuck_as_sarah



Category: Supernatural
Genre: Angry Dean Winchester, Angry John, Choking, Crossdressing, Dirty Dancing, Drug Use, Feminization, First Kiss, Jealousy, Kissing, M/M, Memories, Underage Kissing, Understanding John, very light choking
Language: English
Status: In-Progress
Published: 2015-02-10
Updated: 2015-03-04
Packaged: 2018-03-11 12:36:44
Rating: Not Rated
Warnings: Underage
Chapters: 2
Words: 3,002
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/3327269
Author URL: https://archiveofourown.org/users/stuck_as_sarah/pseuds/stuck_as_sarah
Summary: <blockquote class="userstuff">
              <p>Who knew a skirt and some make up could make you feel so good.</p>
            </blockquote>





	1. James

It was one of the warmer nights in New Orleans. Lights lit up the streets as a group of guys laughed on their way to a club nearby called Tight Rope. James never questioned where his friends decided to go for the weekend. It became a routine to go out Saturday and usually end up taking care of his drunk friends and apologizing to the women they harass. They walked in, immediately sighing at the relief of air conditioning. Blue and purple light flashed along with the music. They pushed their way to the bar and ordered everyone a shot to start. Everyone agreed they'd walk home or get a hotel this time so James could actually drink. The last five times he was the designated driver even though they promised a rotation system when they first started going out. James could only think about how loud and crappy the music was until he got wasted enough to dance.  
With a group of five guys the last thing they talk about doing is dancing. James enjoys dancing the most, but he'll go along with the guys bragging about the chicks they'll pick up this time. After the third round and a few pats to the back James dragged his feet to the middle of the dance floor where there was enough space between people for him to feel comfortable. He was too drunk to think about anything, but the repeating beat of the songs. James swayed his hips and raised his hands over his head, moving to the music. Even though his friends have made fun of how he dances it's the best part of these outings. James really gets into it once he gets drunk and this time he doesn't have to constantly look around the room for where each of his friends are off to.  


James had his eyes closed until something tapped his shoulder. “Hey James! Man, look what I scored!” His friend stood close in the crowded room, shouting in his ear. He could feel heat creeping up on every inch of his body. His stomach ached and there was sweat on his brow from the alcohol. James only looked down when his friend shouted, “You want one too?” His palm was held slightly open to show a few white pills. “Is that X?” James asked. His friend just raised his brows as he put one on his tongue and took another shot to wash it down. “We are going to regret this tomorrow!” James copied his friend and laughed when he said, “Yeah. We'll regret it when we wake up on the sidewalk!”  


At first James just felt sweat prickling all over his body. The tight quarters and loud music caused the room to spin or maybe that was just the alcohol. The song switched and James eyes rolled back. He put his arms back up and moved his hips again. James felt light as he moved. It felt like his head weighed less, but each brush of a shoulder or hip shot sparks through him. This is nothing like anything he's felt. He folded his hands behind his head and tilted up his chin. Blonde locks fell and tickled his cheek, a few strands stuck to his forehead. The ceiling was almost like stars, the flashing lighting made it feel ethereal. He really was floating. James danced till he felt beads of sweat cooling on his skin. He almost jumped when he felt the slightest tickle against his forearm. It was a tall woman with long brunette hair down her back. She kept up the brush of her finger and smiled at the ease of his eyelids.  


“You're really out of it, aren't you?” She spoke softly, leaning close to his ear. James just smiled up at her. “Yeah. You're really tall, aren't you?” He slurred, laughing at himself. Yeah, he must be out of it. The girl in front of him almost glowed. Her skin was tanned and her pink cheeks were framed by the small curls at the front of her hair. She laughed and her white smile stunned him. He felt almost physical effected just looking at her. By the way he stared she must have been able to tell. “I was going to ask you if I could get you a drink, but I'm sure you don't want one,” she told him. James smiled and pushed his hair back to get a moment and gather his thoughts. “Yeah. I probably shouldn't. Do, do you want to dance or something?” She nodded and accepted his hand.  


His eye level went up to her nose. James only thought about it a moment before she eased into his space. She moved her hips slightly, swaying her arms and reaching towards him. Her hands grasp his hips and pulled him in to move against her. He rested his palms on her shoulders and looked up at her with confusion. She leaned down to hear him stutter out, “I, I didn't ask for your name.” She looked amused when she pulled back. Her cheek rested against his and he lifted his chin to feel her lips graze his ear. “I'm Sam.” James held his eyes closed at the euphoric feel of her breath. “I'm James,” he replied finally. The stood still a moment before she turned to sway her hips in front of him. He froze at the sight of her. She closed her eyes and moved her body, hands pushing her long hair back. He stood staring at her dance until she opened her eyes and smiled at him over her shoulder. Sam turned and reached for his arms, leaning to talk to him. “Just dance like you were before. You looked so peaceful.” She let go to turn and shimmy her hips while glancing at him. James stepped towards her and tentatively rested his hands on her. Once they connected Sam reached an arm back to hold his hips to her as they moved.  


They flowed together through each song. Sam tilted her head back to rest on his shoulder, lifted a hand to drag through his short hair. They kept moving, feeling each others bodies so close. Her hair cascaded down the side of her head, baring her neck. James reached around her, brushing his fingers up to rest his hand on her neck, holding her head to the side before moving his lips against her. He felt her ease into his grasp at his hot breath. James held onto her when took a first bite. Sam's knees barely held up, their movements slowed to slow grinding. He moved up her neck, sucking and biting his way up and down. James pulled back, moving his hand to turn her chin towards him. Her eyelids were just as at ease as his now. The kiss was messy at the angle, open mouth, tongues twirling. They only stopped once Sam turned and gave a small push to his chest. “I, I can't-” she started before a big burly man shoulder her back a foot and continued on walking. James was about to reach towards the guy and turn him around, maybe even throw a punch. He wasn't sure in the moment. A woman shoved by them so quick James couldn't catch a face, but he heard a yelp from Sam. She reached towards the other woman just barely too slow. “Dean!”  


James almost missed her reaching towards the waist band of her skirt revealing a pistol she was most definitely about to put to the man's head. The only thing that stopped her was Sam's hand at her wrist. Her hand hesitated on the gun before hiding it under her blouse and resigning to being dragged away by Sam. The last moment he had with Sam was when she turned to him and he thinks he heard her say that he was beautiful before kissing him goodbye. He never told his friends all that happened, but he won't forget it anytime soon.


	2. Floral Print

**Summary for the Chapter:**

> Sam remembers the first dress Dean bought him.

“Dean, what the fuck was that?” Sam yelled once Dean had finished dragging him back to the motel. “Sammy, that dude didn't even apologize! Let alone thinking he was bumping into a lady like that.” Dean drifted off, turning away from Sam. He was pulling off his short blonde wig and running a hand through his hair. Every time they got back from their nights out Dean changed instantly unlike Sam, who fancied wearing a skirt around and sometimes a cute blouse. He couldn't deny the wigs were a bit itchy sometimes. Sam sighed before following and removing his long fake brown hair and combing through his own hair. Sam used to steal skirts and lacy tops until Dean came to pick him up from a store threatening to call the cops. Dean ended up flirting with the owner and eventually screwing her to get her to let it slide. He always did know how to get away with things.  


It was only when Dean defended him when John caught Sam wearing a red skirt he was very fond of that Sam knew he could really always be like this with him. He would often spin and watch as the creases mended and flew together seamlessly as if he was a princess. John had called him all sorts of things that night, even blamed Dean and called him perverted, Sam could never forget. He'd slammed Dean to a wall and demanded to know what he'd done to him. Even though John stormed off, he came back after a few drinks, slipping in next to Sam, still young and laying in wait on the couch. John had lifted Sam's small head and rested it against his thigh, brushing hair from his face. When Sam started to stir John just shushed him and soothed a hand against his scalp. “I'm sorry Dad,” Sam spoke, hardly a whisper, hesitating to turn and meet John's eyes. Sam remembers the small smile and the sad look in his eyes. John just shook his head and replied, “You don't have to apologize to me, ever.”  


Even though John wouldn't comment when Sam wore the occasional blouse or dress, he still rarely dressed up around him. It was less fun than he felt it should have been, less fun than when it was just him and Dean. Sam at first teased Dean, assuming he wished he could wear skirts too. He even would tell Dean how cute he'd look in them, earning a response of 'Fuck you' each time. Sam still caught the blush on his cheeks. It wasn't till a night Dean acted angrier than usual at John leaving on a hunt and claiming as he did each time to 'Take care of Sammy.' Sam had a new dress Dean had picked out for him with a pretty floral print over a knee length white with ruffles towards the bottom and lace around the top. He'd thought changing into the dress Dean had just got would make him happy, even start some dinner, of course with his favorite apron keeping it safe. When he stepped out of their room Dean hadn't even glanced up from his magazine, the headphones on his tape player probably zoning out the sound of the door. Sam just shrugged it off and began cooking some pasta, deciding to go all out for Dean since it was his fault Dean was always stuck looking after him. Sam had already put the noodles in some boiling water and was just bending to put a pan with toast and butter into the oven when he heard something crash on the hardwood.  


Dean was staring at Sam, mouth hanging open. Sam's brows knit together and he only responded, “What?” When Dean's eyes dragged down his new outfit Sam snapped out of his confusion, giving a little twirl as he spoke. “Oh, yeah. Do you like it, Dean? It was a great choice, knew I'd look so pretty in it. Don't worry I won't get any sauce on it I swear.” Dean made a choked off noise in his throat as the smallest bit of Sam's upper thighs showed with his casual spin. He'd looked away fast and threw his legs off the end of the couch, assessing the damage to his tape player on the ground. Sam was draining the water out of the pot of pasta when Dean had thrown the already broken player at the wall, pieces of it flying everywhere. The noise frightened Sam and he fumbled with the pot in the sink, dropping the oven mitts in and still reaching for the scalding handles. “Shit!” Sam had sworn. Dean already had his head in his hands, gathering himself until he heard Sam curse. He burst up to scold him for it before he took in the scene. As Sam saw Dean approaching him he stumbled with his words, struggling with the oven mitts before giving up and backing into the counter. “I-I'm sorry, Dean. I'm s-sorry,” Sam was staring at the floor, attempting to control the coming tears as he grasped the burns on his finger tips.  


Sam felt nausea grow in the pit of his stomach with each step closer Dean got. Once he built up the nerve to look at Dean the tears fell and the only thing he could think to choke out was, “I got your dress wet.” Even now Sam thinks to how scared he was until he saw the soft look in Dean's eyes and the matching fear on the surface instead of layers deep. “Dean, I'm s-,” Sam tried, quieting at the hesitant touch of hands to tear stained cheeks, cradling his head. Sam almost felt like Dean could read his mind. In that moment Sam thought how easy it'd be for Dean to just end his short life right there, how his life was and always will be in Dean's hands and Dean had simply hushed out, “You know I'd never hurt you,” brushing off the tears. Sam looked down to his hands and once he had Dean grabbed his wrists, turning them palms up. He'd never forget how Dean had ever so lightly grazed the tips on his fingers up his palm till he heard a hiss from Sam at the smallest touch to a burnt red finger. Without thinking Dean brought it to his tongue and soothed the burn as he would with paper cuts and splinters, but this felt completely new, a new kind of intimacy. Sam felt a stirring in his stomach, now not from nausea, a fluttering at the cool feel of Dean's saliva taking away the sting of the burn.  


Dean stared right through him, moving his tongue around the finger. Sam brushed the two other red finger tips against Dean's chapped lips, scrunching his face at the pain. He'd instantly opened to sooth the others, gently rubbing his tongue against them. It felt like a full hour before Sam eased his pruned fingers from Dean's mouth. He had followed them as if he himself needed to be soothed by the knowledge of making Sam feel better. Crowded against the counter, Sam started to feel again where it pressed into his lower back. “Dean...” Sam choked, rasping the words out. He was convinced then Dean _could_ read his mind. They acted as one the moment Sam lifted to the tips of his toes to reach Dean's lips, crashing together. Their two amateur mouths meshing unsystematic. Dean took control and his strong hand held onto all of Sam's small neck, slowing their pace. Sam stirred at the thought of how easily Dean could just crush him, hold a hand tight around his neck yet instead holding him closer, keeping him in place.  


On bad days Sam thinks back to their first time, his little body lifted in Dean's rough hands, the chill of the counter on his bare thighs, the first feel of Dean's cock against his own. The memory stopped Sam on his way to the motel's bathroom. He looked over his shoulder with a smirk and poked once more at the subject. “Just be honest Dean. You were jealous. That guy was pretty hot and he really did want me. I was even thinking about telling him about me. I'd probably still get in his pants after he knew I had a dick.” Sam turned at the first sign of a grow, ready for Dean's few large strides across the room. He braced for the shove against the wall, the strong grasp at his neck rousing a warmth beneath his skirt. “Shut. Up.” Dean grit through his teeth, angrier at each second of Sam's smug grin pointed at him. Sam's gaze darkened, begging Dean to read his mind again. He wanted this, he was warmed up for this. Show how much you want me, his eyes begged. Tell me I'm yours and only yours, they told Dean. He flexed and squeezed once at Sam's neck before easing up and running his thumb against the line of Sam's jaw.  


“Would've brought him back here, would've fucked him with you Dean,” Sam pressed. Dean shook his head, looking so young again, giving soft caress', feeling his way on Sam's face as if that's all he would ever want to feel, to relearn, just _Sam_. “I don't want him, I just want you Sammy.” It felt as soft as the night he lost his virginity to Dean. Each little touch was Dean's hands worshiping his body, every small graze had his nerves singing, his brain sparking with each memory brought back. Every painful moment soothed with Dean's lips. Even now something fluttered in Sam when Dean cradled his head, held on tight to his neck, deciding Sam was worth it. Telling him to stay without needing to speak the words. Sam thought of the floral print dress, stuffed into his duffle even now, forever with him holding the memory just as he would.


End file.
